DE2548061C2 - - Google Patents
Info
- Publication number
- DE2548061C2 DE2548061C2 DE2548061A DE2548061A DE2548061C2 DE 2548061 C2 DE2548061 C2 DE 2548061C2 DE 2548061 A DE2548061 A DE 2548061A DE 2548061 A DE2548061 A DE 2548061A DE 2548061 C2 DE2548061 C2 DE 2548061C2
- Authority
- DE
- Germany
- Prior art keywords
- polymerization
- hydroxyethyl methacrylate
- heated
- mixture
- hours
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000006116 polymerization reaction Methods 0.000 claims description 44
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 24
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 23
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 claims description 12
- 239000003112 inhibitor Substances 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 238000005266 casting Methods 0.000 claims description 7
- 239000003505 polymerization initiator Substances 0.000 claims description 6
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 5
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 5
- 239000011261 inert gas Substances 0.000 claims description 5
- 229960003505 mequinol Drugs 0.000 claims description 5
- 239000000178 monomer Substances 0.000 claims description 5
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- UICXTANXZJJIBC-UHFFFAOYSA-N 1-(1-hydroperoxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(OO)CCCCC1 UICXTANXZJJIBC-UHFFFAOYSA-N 0.000 claims description 2
- 238000010521 absorption reaction Methods 0.000 claims 1
- 239000008240 homogeneous mixture Substances 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- -1 hydroxyethyl methacrylate Hydroquinone methyl ether Chemical compound 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 230000036571 hydration Effects 0.000 description 5
- 238000006703 hydration reaction Methods 0.000 description 5
- 239000002504 physiological saline solution Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000010559 graft polymerization reaction Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000003999 initiator Substances 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 229920006267 polyester film Polymers 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 238000012662 bulk polymerization Methods 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 238000005520 cutting process Methods 0.000 description 2
- 238000007872 degassing Methods 0.000 description 2
- 229940061607 dibasic sodium phosphate Drugs 0.000 description 2
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229940045641 monobasic sodium phosphate Drugs 0.000 description 2
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 2
- 235000019799 monosodium phosphate Nutrition 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920002338 polyhydroxyethylmethacrylate Polymers 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 201000009310 astigmatism Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 239000008366 buffered solution Substances 0.000 description 1
- NSGQRLUGQNBHLD-UHFFFAOYSA-N butan-2-yl butan-2-yloxycarbonyloxy carbonate Chemical compound CCC(C)OC(=O)OOC(=O)OC(C)CC NSGQRLUGQNBHLD-UHFFFAOYSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 201000006318 hyperopia Diseases 0.000 description 1
- 230000004305 hyperopia Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 208000001491 myopia Diseases 0.000 description 1
- 230000004379 myopia Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000011236 particulate material Substances 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 238000009849 vacuum degassing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/07—Stiffening bandages
- A61L15/12—Stiffening bandages containing macromolecular materials
- A61L15/125—Mixtures of macromolecular compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/42—Use of materials characterised by their function or physical properties
- A61L15/44—Medicaments
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
- B29D11/00—Producing optical elements, e.g. lenses or prisms
- B29D11/00009—Production of simple or compound lenses
- B29D11/00038—Production of contact lenses
- B29D11/00067—Hydrating contact lenses
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
- B29D11/00—Producing optical elements, e.g. lenses or prisms
- B29D11/00009—Production of simple or compound lenses
- B29D11/00038—Production of contact lenses
- B29D11/00125—Auxiliary operations, e.g. removing oxygen from the mould, conveying moulds from a storage to the production line in an inert atmosphere
- B29D11/00134—Curing of the contact lens material
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F271/00—Macromolecular compounds obtained by polymerising monomers on to polymers of nitrogen-containing monomers as defined in group C08F26/00
- C08F271/02—Macromolecular compounds obtained by polymerising monomers on to polymers of nitrogen-containing monomers as defined in group C08F26/00 on to polymers of monomers containing heterocyclic nitrogen
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
- G02B1/043—Contact lenses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
Landscapes
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Manufacturing & Machinery (AREA)
- Mechanical Engineering (AREA)
- Ophthalmology & Optometry (AREA)
- Physics & Mathematics (AREA)
- Materials Engineering (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Hematology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Optics & Photonics (AREA)
- Eyeglasses (AREA)
- Graft Or Block Polymers (AREA)
- Casting Or Compression Moulding Of Plastics Or The Like (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Moulds For Moulding Plastics Or The Like (AREA)
- Laminated Bodies (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
- Processing And Handling Of Plastics And Other Materials For Molding In General (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/526,022 US3978164A (en) | 1974-11-21 | 1974-11-21 | Pyrrolidone-methacrylate graft copolymers from 3-stage polymerization process |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2548061A1 DE2548061A1 (de) | 1976-06-10 |
| DE2548061C2 true DE2548061C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-01-14 |
Family
ID=24095603
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752548061 Granted DE2548061A1 (de) | 1974-11-21 | 1975-10-27 | Masse fuer kontaktlinsen bzw. augenverbaende und verarbeitung der masse |
Country Status (7)
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4022204A (en) * | 1974-11-21 | 1977-05-10 | Warner-Lambert Company | Dimensionally stable shaped eye bandages |
| US4127638A (en) * | 1976-09-13 | 1978-11-28 | American Optical Corporation | Process for casting polymer rods |
| US4123408A (en) * | 1976-11-26 | 1978-10-31 | American Optical Corporation | Hydrogel contact lens |
| US4123407A (en) * | 1976-11-26 | 1978-10-31 | American Optical Corporation | Hydrophilic contact lens |
| US4158030A (en) * | 1977-06-24 | 1979-06-12 | Nick Stoyan | Method for making lenses from a modified polymerization product of methyl methacrylate |
| USRE31422E (en) * | 1977-12-27 | 1983-10-18 | Schering Corporation | Hydrophilic polymers and contact lenses of high water content |
| US4500437A (en) * | 1980-12-15 | 1985-02-19 | Cassella Aktiengesellschaft | Water soluble copolymers for use in fracture-acidizing of wells |
| US4507440A (en) * | 1980-12-15 | 1985-03-26 | Cassella Aktiengesellschaft | Cross-linkable and cross linked macromolecular compositions wherein cross-linking is by structural bridges of the formula --NRx --CH═N--CO-- and their preparation |
| US4551513A (en) * | 1980-12-15 | 1985-11-05 | Cassella Aktiengesellschaft | Water soluble copolymers |
| JPS57103525U (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1980-12-17 | 1982-06-25 | ||
| US4499232A (en) * | 1982-07-19 | 1985-02-12 | Cassella Aktiengesellschaft | Water soluble, crosslinkable polymer compositions, their preparation and use |
| DE3243339C2 (de) * | 1982-11-19 | 1986-03-27 | Helmut Dr.med. 2000 Hamburg Opel | Verfahren zur Gewinnung von Tränenflüssigkeit |
| CS267858B1 (en) * | 1987-01-12 | 1990-02-12 | Sulc Jiri | Contact,if need be,intra-ocular lens and method of its production |
| CA1318446C (en) * | 1988-05-31 | 1993-05-25 | William J. Burke | Contact lenses and materials and methods of making same |
| WO1999017917A1 (en) * | 1997-10-02 | 1999-04-15 | Novartis Ag | Ophthalmic lens production process |
| JP5154231B2 (ja) | 2005-02-14 | 2013-02-27 | ジョンソン・アンド・ジョンソン・ビジョン・ケア・インコーポレイテッド | 快適な眼科用具およびその製造法 |
| US20070074980A1 (en) * | 2005-09-02 | 2007-04-05 | Bankoski Brian R | Implant rehydration packages and methods of use |
| US9052529B2 (en) | 2006-02-10 | 2015-06-09 | Johnson & Johnson Vision Care, Inc. | Comfortable ophthalmic device and methods of its production |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3621079A (en) * | 1968-10-21 | 1971-11-16 | Patent Structures Inc | Graft of hydroxyalkyl methacrylate onto polyvinylpyrrolidone |
| US3639524A (en) * | 1969-07-28 | 1972-02-01 | Maurice Seiderman | Hydrophilic gel polymer insoluble in water from polyvinylpyrrolidone with n-vinyl-2-pyrrolidone and methacrylic modifier |
| BE759530A (fr) * | 1969-11-28 | 1971-04-30 | Griffin Lab Inc | Lentille de contact et son procede de fabrication |
| US3822196A (en) * | 1969-11-28 | 1974-07-02 | Warner Lambert Co | Fabrication of soft plastic contact lens blank and composition therefor |
| US3647736A (en) * | 1970-05-25 | 1972-03-07 | Kontur Kontact Lens Co Inc | Hydrophilic contact lens material |
| US3807398A (en) * | 1972-09-19 | 1974-04-30 | B Grucza | Ocular implant |
| US3839304A (en) * | 1973-02-12 | 1974-10-01 | American Optical Corp | Soft contact lens and method of production thereof |
| US3894129A (en) * | 1973-03-15 | 1975-07-08 | American Optical Corp | Method of manufacture of strain free contact lenses |
-
1974
- 1974-11-21 US US05/526,022 patent/US3978164A/en not_active Expired - Lifetime
-
1975
- 1975-10-21 GB GB50300/77A patent/GB1529709A/en not_active Expired
- 1975-10-21 GB GB43133/75A patent/GB1529708A/en not_active Expired
- 1975-10-27 DE DE19752548061 patent/DE2548061A1/de active Granted
- 1975-11-17 JP JP13803475A patent/JPS5318558B2/ja not_active Expired
- 1975-11-17 FR FR7534974A patent/FR2292011A1/fr active Granted
- 1975-11-20 CA CA240,087A patent/CA1076477A/en not_active Expired
-
1977
- 1977-11-25 JP JP14142177A patent/JPS53124569A/ja active Granted
-
1981
- 1981-04-30 HK HK165/81A patent/HK16581A/xx unknown
- 1981-04-30 HK HK166/81A patent/HK16681A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2548061A1 (de) | 1976-06-10 |
| HK16681A (en) | 1981-05-08 |
| GB1529709A (en) | 1978-10-25 |
| JPS5318558B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-06-15 |
| AU8670375A (en) | 1977-06-02 |
| JPS51102653A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-09-10 |
| HK16581A (en) | 1981-05-08 |
| CA1076477A (en) | 1980-04-29 |
| GB1529708A (en) | 1978-10-25 |
| US3978164A (en) | 1976-08-31 |
| JPS53124569A (en) | 1978-10-31 |
| FR2292011B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-02-02 |
| JPS5420543B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-07-24 |
| FR2292011A1 (fr) | 1976-06-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8125 | Change of the main classification |
Ipc: C08F271/02 |
|
| 8127 | New person/name/address of the applicant |
Owner name: AO, INC., SOUTHBRIDGE, MASS., US |
|
| 8128 | New person/name/address of the agent |
Representative=s name: DIEHL, H., DIPL.-PHYS. DR.RER.NAT. KRESSIN, H., DI |
|
| 8128 | New person/name/address of the agent |
Representative=s name: DIEHL, H., DIPL.-PHYS. DR.RER.NAT., PAT.-ANW., 800 |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |